DOCSLIB.ORG

E4 Acids, Bases, and Salts Neutralization

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text

Load more

Acid - Base Neutralization (Parts 3 - 5) E4 Acids, Bases, and Salts Neutralization: HCl(aq) + NH4OH(aq) → NH4Cl(aq) + HOH(l) Session two acid + base → salt + water . Parts 3, 4, and 5 . Complete the team report and discussion presentation. DEMO - proton transfer reaction: HCl(g) + NH3(g) → NH4Cl(s) Carboxylic Acids and Ionizable Protons Carboxylic Acids (Parts 3 - 5) Electronegativity of the elements* 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 VIIIB . Neutralization of carboxylic acids with NaOH IA IIA IIIB IVB VB VIB VIIB IB IIB IIIA IVA VA VIA VIIA H 2.1 Carboxylic acids Li Be B C N O F 1.0 1.5 2.0 2.5 3.0 3.5 4.0 Carboxylic acids contain the group Na Mg Al Si P S Cl 0.9 1.2 1.5 1.8 2.1 2.5 3.0 K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br 0.8 1.0 1.3 1.5 1.6 1.6 1.5 1.8 1.8 1.8 1.9 1.6 1.6 1.8 2.0 2.4 2.8 Rb Sr Y Zr Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb Te I 0.8 1.0 1.2 1.4 1.6 1.8 1.9 2.2 2.2 2.2 1.9 1.7 1.7 1.8 1.9 2.1 2.5 Cs Ba La Hf Ta W Re Os Ir Pt Au Hg Tl Pb Bi Po At .0 .T7 h0e. 9e le-cLtur o1n.3e ga1.t5iv i1t.y7 o1f .H9 a2n.2d 2O.2 d i2f.f2e r2 a.4n d1 .t9h e1r.e8f o1r.e8 H1 .i9n t2h.0e 2.2 CFOr ORHa gArco upT ho f Pca rbUo xyNlipc- a Nciod s is io niza ble. 0.7 0.9 1.1 1.3 1.5 1.7 1.3 . The electronegativity of H and C are similar and therefore C-H b ond=s Me atalrelo isdst ab le and= Ntohnmee tpalrs oto n in =t hMeet aCls -H b ond is NO T ioniz abl e 1 Carboxylic acids Acid-Base Reaction Stoichiometry • H O Part 3: Acetic acid . Reaction stoichiometry is dependant on the number of ionizable • | || HC2H3O2 protons. • H− C − C − O − H CH3COOH Acetic acid (Part 3): • | Carboxylic group containing CH3COOH + NaOH → CH3COONa + HOH one ionizable proton • H 1 mol 1 mol • O O Part 4: Oxalic acid Oxalic acid (Part 4): • || || H2C2O4 HOOC-COOH + 2 NaOH → 2COONa + 2HOH 1 mol 2 mol •H − O− C − C − O − H HOOCCOOH Two carboxylic groups each with one ionizable proton Acid-Base Neutralization Equilibria Titration (Parts 3 - 5) • Adding base to the weak (partially ionized) carboxylic . A procedure for determining the concentration acid drives the reaction (donation of proton/s) to completion of a measured volume of acid (or base) by measuring the volume of base (or acid) of known + - • A Ct nHe3uCtrOalOizHat i o n , o n →ly the Hpr odu+c t s C(sHalt3 CanOdO water) concentration required for neutralization are present. + - . A procedure for determining the identity CH3COOH + NaOH O HCH→3C O HOONHa + HOH of a measured mass of acid (or base) by measuring the volume of base (or acid) of known concentration required for neutralization 2 Titration Q. Identify the acid (acetic or oxalic) if 10.0 mL of 0.10 M NaOH neutralizes 10.0 mL of 0.10 M acid. Acetic acid CH3COOH + NaOH → CH3COONa + HOH Oxalic acid HOOC-COOH + 2 NaOH → 2COONa + 2HOH Answer. Acetic acid. mmol acid = mmol base 10.0 mL • 0.10 M = 10.0 mL • 0.10 M note: 5.0 mL of 0.10 M oxalic acid neutralizes 10.0 mL of 0.10 M NaOH: Base delivered Indicator color change 2 (mmol acid) = mmol base from burette signals the end-point 2 (5.0 mL • 0.10 M) = 10.0 mL • 0.10 M DEMO or neutralization Part 3 Acid-Base Neutralizations and Indicators Indicator End Point pH . Compare the use of three indicators for monitoring the neutralization of acetic acid with sodium hydroxide . The pH interval at which the indicator changes color • Bromothymol blue and bromophenol blue Acids are colorless Bases are pink Acids turn yellow Bases turn blue Phenolphthalein: pH 8.2 - pH 10.1 ↑ • Phenolphthalein pH 9.1 Acids are colorless Bases turn pink . The indicator color change is observable at the mid-point of the end point pH range. 3 Indicator pH End Points Equivalence Point pH . The pH of the salt and water products of the acid-base neutralization reaction = the equivalence point pH. CH3COOH + NaOH → CH3COONa + HOH Equivalence point pH ≈ pH 8 “Ideally, the indicator end point pH equals the equivalence point pH = pH 8. “ DEMO . Indicators have different end-point pH color changes . For information on lab indicators, see the lab manual, p. 183 Titration and Indicator pH End Points Titration of Oxalic Acid (Part 4) Q. You titrate 0.4502 g of oxalic acid with 1.0 M NaOH. How many mL of 1.0 M NaOH are required for neutralization? Oxalic acid: MW = 90.04 HOOC-COOH + 2 NaOH → 2COONa + 2HOH 0.5 mol 1 mol 45.02 g 1 mol (or 1000 mmol) Answer. Fact: 0.4502 g acid will neutralize 10 mmol of NaOH. X mL • 1.0 M NaOH = 10 mmol NaOH X = 10 mL of 1.0 M NaOH 4 See Table, p.110 Part 5. Identification of an Unknown Acid Name Formula MW EW MP 2-hydroxybenzoic 180 180 135 • Identify a carboxylic acid from melting point and COOH titration data acid acetate OCOCH3 • The melting point range will be determined using a melting point apparatus trans-cinnamic acid 148 148 135- CH CH COOH • The equivalent weight will be determined by titrating a 136 known mass of the acid with NaOH 2-chlorobenzoic acid Cl 157 157 140 COOH COOH cis-butenedioic HOOC 116 58 139- H (maleic) acid H 140 Equivalent Weight (EW) Unknowns and Carboxylic Acid Structure Theoretical • Benzoic acid • COOH . EW = Molecular Wt/# ionizable protons • • • . One ionizable proton. Examples: H SO = molecular weight of 98 2 4 Benzoic acid = C6 H5COOH H2SO4 = equivalent weight of 49 HCl = molecular weight of 36.5 MW = EW HCl = equivalent weight of 36.5 . No ionizable protons. Not an acid. 5 Q. An acid has an equivalent weight (EW) of 88.92. The EW = molecular wt/#ionizable protons. List the number of any compound from the table that may be the acid. • O H H H H O Adipic acid • | | | | | | | | HOOC(CH2 )4COOH H - O − C − C − C − C − C − C − O − H Compound Formula MW • | | | | 1. Ethanoic acid CH3COOH 60 • H H H H .Two ionizable protons. 2. Butanoic acid CH3CH2CH2COOH 88 3. Oxalic acid HOOC-COOH 90 Molecular Weight = 146 4. 1-methyl, 1,2 benzene CH3C6H3(COOH)2 180 Equivalent weight = ______7_3______? dicarboxylic acid Answer. Compounds # 2 and # 4. A teammate titrates a carboxylic acid and calculates the EW from Experiment Data (Part 5) EW of the acid to be 72.50. The result is correct within 2%. The MW of the acid is determined to be 1.5 x 102 . Determine the equivalent weight of an unidentified A. How many ionizable protons/mol are in the acid?that carboxylic acid by determining the volume of base of • known concentration required to neutralize a measured Let X = # ionizable protons. mass of the unknown acid EW = 72.50 = MW/X = 150/X X= ~ 2 B. Circle each structure that is consistent with the data. • EW = Mass (g) of acid neutralizing 1 mol OH-. Adipic Acid, MW = 146: Trans-cinnamic acid, MW=148 HO2CCH2CH2CH2CH2CO2H -CH=CH-COOH EW = mass acid (g) moles of OH- neutralized Citric Acid, MW = 192: Oxalic acid, MW = 90 HO2C-CH2-C(OH)-CH2-CO2H HO2C—CO2H CO2H 6 Q. You titrate 0.175 g of an acid. 30.00 mL of 0.10 M EW of Oxalic Acid (Part 4) NaOH neutralizes the sample. 1) What is the acid’s EW based on the data? Q. 10.0 mL of 1.0 M NaOH neutralizes 0.4502 grams of 2) Identify the acid from the list below. oxalic acid, what is the equivalent weight of the acid? Name Formula MW MP Oxalic acid: MW = 90.04 2-hydroxybenzoic acid acetate COOH 180 135 HOOC-COOH + 2 NaOH → 2COONa + 2HOH OCOCH3 0.5 mol 1 mol trans-cinnamic acid 148 135-136 CH CH COOH 45.02 g 1 mol (or 1000 mmol) 2-chlorobenzoic acid Cl 157 140 COOH Answer. 0.4502 g neutralized 10.0 mmol of NaOH. cis-butenedioic (maleic) acid H H 116 139-140 The mass of acid needed to neutralize 1 mol = 45.02g = EW HOOC COOH Equivalent weight determination. Equivalent Weight determination. 1) Determine mol of NaOH the acid has neutralized. 2) Determine the mass of acid that would Known: The acid mass neutralized 30.00 mL of 0.10 M NaOH neutralize one mol of hydroxide ions. - mol OH = V(L) x M NaOH - Known: 0.175 g = 0.0030 mol OH - X g acid 1 mol OH = 0.0300L x 0.10 mol L X = 58 g = 3.0 x 10-3 mol 7 Q. What is the identity of the acid? Name Formula MW MP 2-hydroxybenzoic acid acetate COOH 180 135 OCOCH3 trans-cinnamic acid 148 135-136 CH CH COOH 2-chlorobenzoic acid Cl 157 140 COOH Questions? cis-butenedioic (maleic) acid √ H H 116 139-140 Contact [email protected] HOOC COOH 8.
Recommended publications
  • Chapter 21 the Chemistry of Carboxylic Acid Derivatives

    Chapter 21 the Chemistry of Carboxylic Acid Derivatives

    Instructor Supplemental Solutions to Problems © 2010 Roberts and Company Publishers Chapter 21 The Chemistry of Carboxylic Acid Derivatives Solutions to In-Text Problems 21.1 (b) (d) (e) (h) 21.2 (a) butanenitrile (common: butyronitrile) (c) isopentyl 3-methylbutanoate (common: isoamyl isovalerate) The isoamyl group is the same as an isopentyl or 3-methylbutyl group: (d) N,N-dimethylbenzamide 21.3 The E and Z conformations of N-acetylproline: 21.5 As shown by the data above the problem, a carboxylic acid has a higher boiling point than an ester because it can both donate and accept hydrogen bonds within its liquid state; hydrogen bonding does not occur in the ester. Consequently, pentanoic acid (valeric acid) has a higher boiling point than methyl butanoate. Here are the actual data: INSTRUCTOR SUPPLEMENTAL SOLUTIONS TO PROBLEMS • CHAPTER 21 2 21.7 (a) The carbonyl absorption of the ester occurs at higher frequency, and only the carboxylic acid has the characteristic strong, broad O—H stretching absorption in 2400–3600 cm–1 region. (d) In N-methylpropanamide, the N-methyl group is a doublet at about d 3. N-Ethylacetamide has no doublet resonances. In N-methylpropanamide, the a-protons are a quartet near d 2.5. In N-ethylacetamide, the a- protons are a singlet at d 2. The NMR spectrum of N-methylpropanamide has no singlets. 21.9 (a) The first ester is more basic because its conjugate acid is stabilized not only by resonance interaction with the ester oxygen, but also by resonance interaction with the double bond; that is, the conjugate acid of the first ester has one more important resonance structure than the conjugate acid of the second.
  • Oxalic Acid As a Heterogeneous Ice Nucleus in the Upper Troposphere and Its Indirect Aerosol Effect” by B

    Oxalic Acid As a Heterogeneous Ice Nucleus in the Upper Troposphere and Its Indirect Aerosol Effect” by B

    Atmos. Chem. Phys. Discuss., 6, S1765–S1768, 2006 Atmospheric www.atmos-chem-phys-discuss.net/6/S1765/2006/ Chemistry ACPD c Author(s) 2006. This work is licensed and Physics 6, S1765–S1768, 2006 under a Creative Commons License. Discussions Interactive Comment Interactive comment on “Oxalic acid as a heterogeneous ice nucleus in the upper troposphere and its indirect aerosol effect” by B. Zobrist et al. B. Zobrist et al. Received and published: 13 July 2006 The authors would like to thank anonymous referee #1 for his/her constructive comments. We have addressed the referee’s concerns point-by-point below. Full Screen / Esc Succinic and Adipic acid as immersion IN: The solubility of these dicarboxylic acids is very low at temperatures of about 235 K, Printer-friendly Version as supported by the deliquescence measurements of Parsons et al. (JGR 109, D06212, 2004) which are close to 100 % RH. In our experiments, the droplets of Interactive Discussion these acids are completely liquid in the first cooling cycle with concentrations of Discussion Paper 7.3 wt% for succinic acid and 1.6 wt% for adipic acid, which is why they nucleate ice S1765 EGU homogeneously at temperatures below that of pure water. When the acids precipitate, the concentration of the remaining liquid corresponds to the equilibrium solubility at ACPD each temperature when the samples are cooled in the second cycle. Because of the 6, S1765–S1768, 2006 low solubility at lower temperatures we expect the observed rise in the homogeneous ice nucleation temperature when compared to the first cooling run. In fact, if we use the measured freezing temperatures and assume they are due to homogeneous ice Interactive nucleation, we can use water-activity-based ice nucleation theory to deduce the water Comment activity of the liquid part of the samples.
  • Green Chemistry Accepted Manuscript

    Green Chemistry Accepted Manuscript

    Green Chemistry Accepted Manuscript This is an Accepted Manuscript, which has been through the Royal Society of Chemistry peer review process and has been accepted for publication. Accepted Manuscripts are published online shortly after acceptance, before technical editing, formatting and proof reading. Using this free service, authors can make their results available to the community, in citable form, before we publish the edited article. We will replace this Accepted Manuscript with the edited and formatted Advance Article as soon as it is available. You can find more information about Accepted Manuscripts in the Information for Authors. Please note that technical editing may introduce minor changes to the text and/or graphics, which may alter content. The journal’s standard Terms & Conditions and the Ethical guidelines still apply. In no event shall the Royal Society of Chemistry be held responsible for any errors or omissions in this Accepted Manuscript or any consequences arising from the use of any information it contains. www.rsc.org/greenchem Page 1 of 21 Green Chemistry Green Chemistry RSCPublishing CRITICAL REVIEW Catalytic Routes towards Acrylic Acid, Adipic Acid and ε-Caprolactam starting from Biorenewables Cite this: DOI: 10.1039/x0xx00000x Rolf Beerthuis, Gadi Rothenberg and N. Raveendran Shiju* Received 00th January 2012, The majority of bulk chemicals are derived from crude oil, but the move to biorenewable resources is Accepted 00th January 2012 gaining both societal and commercial interest. Reviewing this transition, we first summarise the types of today’s biomass sources and their economical relevance. Then, we assess the biobased productions DOI: 10.1039/x0xx00000x of three important bulk chemicals: acrylic acid, adipic acid and ε-caprolactam.
  • APPENDIX G Acid Dissociation Constants

    APPENDIX G Acid Dissociation Constants

    harxxxxx_App-G.qxd 3/8/10 1:34 PM Page AP11 APPENDIX G Acid Dissociation Constants §␮ ϭ 0.1 M 0 ؍ (Ionic strength (␮ † ‡ † Name Structure* pKa Ka pKa ϫ Ϫ5 Acetic acid CH3CO2H 4.756 1.75 10 4.56 (ethanoic acid) N ϩ H3 ϫ Ϫ3 Alanine CHCH3 2.344 (CO2H) 4.53 10 2.33 ϫ Ϫ10 9.868 (NH3) 1.36 10 9.71 CO2H ϩ Ϫ5 Aminobenzene NH3 4.601 2.51 ϫ 10 4.64 (aniline) ϪO SNϩ Ϫ4 4-Aminobenzenesulfonic acid 3 H3 3.232 5.86 ϫ 10 3.01 (sulfanilic acid) ϩ NH3 ϫ Ϫ3 2-Aminobenzoic acid 2.08 (CO2H) 8.3 10 2.01 ϫ Ϫ5 (anthranilic acid) 4.96 (NH3) 1.10 10 4.78 CO2H ϩ 2-Aminoethanethiol HSCH2CH2NH3 —— 8.21 (SH) (2-mercaptoethylamine) —— 10.73 (NH3) ϩ ϫ Ϫ10 2-Aminoethanol HOCH2CH2NH3 9.498 3.18 10 9.52 (ethanolamine) O H ϫ Ϫ5 4.70 (NH3) (20°) 2.0 10 4.74 2-Aminophenol Ϫ 9.97 (OH) (20°) 1.05 ϫ 10 10 9.87 ϩ NH3 ϩ ϫ Ϫ10 Ammonia NH4 9.245 5.69 10 9.26 N ϩ H3 N ϩ H2 ϫ Ϫ2 1.823 (CO2H) 1.50 10 2.03 CHCH CH CH NHC ϫ Ϫ9 Arginine 2 2 2 8.991 (NH3) 1.02 10 9.00 NH —— (NH2) —— (12.1) CO2H 2 O Ϫ 2.24 5.8 ϫ 10 3 2.15 Ϫ Arsenic acid HO As OH 6.96 1.10 ϫ 10 7 6.65 Ϫ (hydrogen arsenate) (11.50) 3.2 ϫ 10 12 (11.18) OH ϫ Ϫ10 Arsenious acid As(OH)3 9.29 5.1 10 9.14 (hydrogen arsenite) N ϩ O H3 Asparagine CHCH2CNH2 —— —— 2.16 (CO2H) —— —— 8.73 (NH3) CO2H *Each acid is written in its protonated form.
  • Production of Adipic Acid from Mixtures of Cyclohexanol-Cyclohexanone Using Polyoxometalate Catalysts

    Production of Adipic Acid from Mixtures of Cyclohexanol-Cyclohexanone Using Polyoxometalate Catalysts

    Makara J. Sci. 19/2 (2015), 85-90 doi: 10.7454/mss.v19i2.4778 Production of Adipic Acid from Mixtures of Cyclohexanol-Cyclohexanone using Polyoxometalate Catalysts Aldes Lesbani 1*, Sumiati 1, Mardiyanto 2, Najma Annuria Fithri 2, and Risfidian Mohadi 1 1. Department of Chemistry, Faculty of Mathematic and Natural Sciences, Universitas Sriwijaya, Indralaya (OI), Sumatera Selatan 30662, Indonesia 2. Department of Pharmacy, Faculty of Mathematic and Natural Sciences, Universitas Sriwijaya, Indralaya (OI), Sumatera Selatan 30662, Indonesia *E-mail: [email protected] Abstract Adipic acid production through catalytic conversion of cyclohexanol-cyclohexanone using polyoxometalate H 5[α-BW 12 O40 ] and H 4[α-SiW 12 O40 ] as catalysts was carried out systematically. Polyoxometalates H 5[α-BW 12 O40 ] and H 4[α-SiW 12 O40 ] were synthesized using an inorganic synthesis method and were characterized using Fourier transform infrared spectroscopy (FTIR). Adipic acid was formed from conversion of cyclohexanol-cyclohexanone and was characterized by using melting point measurement, identification of functional group using FTIR spectrophotometer, analysis of gas chromatography-mass spectrometry (GC-MS), and 1H and 13 C NMR (nuclear magnetic resonance) spectrophotometer. This research investigated the influence of reaction time and temperature on conversion. The results showed that adipic acid was formed successfully with a yield of 68% by using H 5[α-BW 12 O40 ] as catalyst at the melting point of 150-152 °C after optimization. In contrast, using H 4[α-SiW 12 O40 ] as catalyst, formation of adipic acid was only 3.7%. Investigation of time and temperature showed 9 h as the optimum reaction time and 90 °C as the optimum temperature for conversion of up to 68% adipic acid.
  • Achieving REACH Compliance for Reaction Products of Acetic Anhydride and Adipic Acid Used in Starch Modifaction

    Achieving REACH Compliance for Reaction Products of Acetic Anhydride and Adipic Acid Used in Starch Modifaction

    Achieving REACH compliance for reaction products of acetic anhydride and adipic acid used in starch modifaction Whitepaper This whitepaper is about the REACH registration of reaction products of acetic anhydride and adipic acid which are commonly used in the acetylation and Cross-Binding of starch based materials. By drs. ing. M. de Kraa AD International BV 04 - 2017 Version 1.2 REACH REGISTRATION:REACTION PRODUCTS OF ACETIC ANHYDRIDE AND ADIPIC ACID ABOUT THE AUTHOR Name: Drs. ing. Marco de Kraa Role: SHEQ Manager Contact: [email protected] Expertise: REACH registration dossier preparation, REACH SDS, chemical classification and labelling in according to CLP, C&L notification, GHS. Marco de Kraa graduated from the University of Leiden with a degree in Analytical Chemistry. In his career at AD International BV Marco has worked in various roles, starting in R&D, later as a laboratory manager and now for more then 15 years as SHEQ Manager. Marco has followed the debates and progress of REACH from the early stages and has more than seven years of knowledge to ensure successful REACH implementation. He supports the objectives of REACH and continuously works on REACH compliance matters at AD International BV. COLOFON This white paper is made by AD International BV [email protected] www.adinternationalbv.com Copyright © 2017 AD International BV. Specifications and designs are subject to change without notice. Non-metric weights and measurements are approximate. All data were deemed correct at time of creation. AD International BV is not liable for errors or omissions. All brand, product, service names and logos are trademarks and/or registered trademarks of their respective owners and are hereby recognized and acknowledged.
  • New Solvent and Coagulating Agent for Development of Chitosan Fibers by Wet Spinning

    New Solvent and Coagulating Agent for Development of Chitosan Fibers by Wet Spinning

    polymers Article New Solvent and Coagulating Agent for Development of Chitosan Fibers by Wet Spinning Ghasem Mohammadkhani 1, Sunil Kumar Ramamoorthy 1 , Karin H. Adolfsson 2, Amir Mahboubi 1 , Minna Hakkarainen 2 and Akram Zamani 1,* 1 Swedish Centre for Resource Recovery, University of Borås, 501 90 Borås, Sweden; [email protected] (G.M.); [email protected] (S.K.R.); amir.mahboubi_soufi[email protected] (A.M.) 2 Department of Fibre and Polymer Technology, KTH Royal Institute of Technology, 100 44 Stockholm, Sweden; [email protected] (K.H.A.); [email protected] (M.H.) * Correspondence: [email protected] Abstract: Adipic acid was evaluated as a novel solvent for wet spinning of chitosan fibers. A solvent with two carboxyl groups could act as a physical crosslinker between the chitosan chains, resulting in improved properties of the fibers. The performance of adipic acid was compared with conventional solvents, i.e., lactic, citric, and acetic acids. Chitosan solutions were injected into a coagulation bath to form monofilaments. Sodium hydroxide (NaOH) and its mixture with ethanol (EtOH) were used as coagulation agents. Scanning electron microscopy confirmed the formation of uniform chitosan monofilaments with an even surface when using adipic acid as solvent. These Citation: Mohammadkhani, G.; monofilaments generally showed higher mechanical strength compared to that of monofilaments Kumar Ramamoorthy, S.; Adolfsson, produced using conventional solvents. The highest Young’s modulus, 4.45 GPa, was recorded for K.H.; Mahboubi, A.; Hakkarainen, M.; adipic acid monofilaments coagulated in NaOH-EtOH. This monofilament also had a high tensile Zamani, A. New Solvent and Coagulating Agent for Development strength of 147.9 MPa.
  • Adipic Acid Production Protocol Version 1.0, September 2020

    Adipic Acid Production Protocol Version 1.0, September 2020

    Adipic Acid Production Protocol | Version 1.0 |September 30, 2020 Climate Action Reserve www.climateactionreserve.org Released September 30, 2020 © 2020 Climate Action Reserve. All rights reserved. This material may not be reproduced, displayed, modified, or distributed without the express written permission of the Climate Action Reserve. Adipic Acid Production Protocol Version 1.0, September 2020 Acknowledgements Staff (alphabetical) Trevor Anderson Max DuBuisson Craig Ebert Sami Osman Heather Raven Jonathan Remucal Sarah Wescott Workgroup The list of workgroup members below comprises all individuals and organizations that have advised the Reserve in developing this protocol. Their participation in the Reserve process is based on their technical expertise and does not constitute endorsement of the final protocol. The Reserve makes all final technical decisions and approves final protocol content. For more information, see section 4.2.1 of the Reserve Offset Program Manual. Seth Baruch Carbonomics, LLC Phillip Cunningham Ruby Canyon Engineering, Inc William Flederbach ClimeCo Corporation John McDougal Element Markets Lambert Schneider Öko-Institut Financial and Technical Support This document was developed with financial support and technical support from ClimeCo Corporation. William Flederbach Lauren Mechak Tip Stama Scott Subler Jim Winch Adipic Acid Production Protocol Version 1.0, September 2020 Table of Contents Abbreviations and Acronyms .....................................................................................................
  • Dissociation Constants of Organic Acids and Bases

    Dissociation Constants of Organic Acids and Bases

    DISSOCIATION CONSTANTS OF ORGANIC ACIDS AND BASES This table lists the dissociation (ionization) constants of over pKa + pKb = pKwater = 14.00 (at 25°C) 1070 organic acids, bases, and amphoteric compounds. All data apply to dilute aqueous solutions and are presented as values of Compounds are listed by molecular formula in Hill order. pKa, which is defined as the negative of the logarithm of the equi- librium constant K for the reaction a References HA H+ + A- 1. Perrin, D. D., Dissociation Constants of Organic Bases in Aqueous i.e., Solution, Butterworths, London, 1965; Supplement, 1972. 2. Serjeant, E. P., and Dempsey, B., Ionization Constants of Organic Acids + - Ka = [H ][A ]/[HA] in Aqueous Solution, Pergamon, Oxford, 1979. 3. Albert, A., “Ionization Constants of Heterocyclic Substances”, in where [H+], etc. represent the concentrations of the respective Katritzky, A. R., Ed., Physical Methods in Heterocyclic Chemistry, - species in mol/L. It follows that pKa = pH + log[HA] – log[A ], so Academic Press, New York, 1963. 4. Sober, H.A., Ed., CRC Handbook of Biochemistry, CRC Press, Boca that a solution with 50% dissociation has pH equal to the pKa of the acid. Raton, FL, 1968. 5. Perrin, D. D., Dempsey, B., and Serjeant, E. P., pK Prediction for Data for bases are presented as pK values for the conjugate acid, a a Organic Acids and Bases, Chapman and Hall, London, 1981. i.e., for the reaction 6. Albert, A., and Serjeant, E. P., The Determination of Ionization + + Constants, Third Edition, Chapman and Hall, London, 1984. BH H + B 7. Budavari, S., Ed., The Merck Index, Twelth Edition, Merck & Co., Whitehouse Station, NJ, 1996.
  • A Convenient and Efficient Protocol for the Synthesis of Adipic Acid Catalyzed by ACC/Silica Gel Under Ultrasound Irradiation

    A Convenient and Efficient Protocol for the Synthesis of Adipic Acid Catalyzed by ACC/Silica Gel Under Ultrasound Irradiation

    ISSN: 0973-4945; CODEN ECJHAO E-Journal of Chemistry http://www.ejchem.net 2012, 9(3), 1035-1035 A Convenient and Efficient Protocol for the Synthesis of Adipic Acid Catalyzed by ACC/Silica Gel under Ultrasound Irradiation ZHI-PING LIN Department of Biology and Chemistry, Baoding University, Baoding 071000, P. R. China. [email protected] Received 10 November 2011; Accepted 15 January 2012 Abstract: Adipic acid was synthesized from cyclohexanol oxidized by ACC/silica gel in 89% yield within 3 h at 300C under ultrasound irradiation. Keywords: adipic acid; ACC/silica gel; synthesis; ultrasound irradiation. Introduction Adipic acid is a most important organic synthetic intermediate, and mainly used for synthetic fibers: nylon-66, other fields can also be widely used, for example polyurethane, synthetic resin, leather, polyester foam, plastic plasticizers, lubricants, food additives, adhesives, pesticides, dyes, spices, medicine 1. The adipic acid was synthesized usually throughout the oxidation of cyclohexene, cyclohexanol, cyclohexanone or a mixture of them or electro-oxidation of cyclohexanol 2, with nitric acid, potassium permanganate, molecular oxygen, ozone, sodium hypochlorite 3 as the oxidant. Much attention has been paid for its green synthesis process because of disadvantages in current technology. Hydrogen peroxide as a safe, gentle, clean, cheap and readily available oxidant, can replace traditional high-polluting oxidants in organic synthesis. But in these procedures, the expensive and complex catalysts for example, peroxotungstates and peroxomolybdates 4, ZSM-5 supported metal ions (M/ZSM-5) and N-hydroxyphthalimide (NHPI) 5, heteropoly complexes 6, a carbon supported platinum catalyst 7, Ti-AlSBA15 catalysts 8, manganese diimine catalysts 9, Co-substituted β-zeolites catalysts 10, Iron- phthalocyanine on zeolite Y 11, tungstic acid/acidic organic additive 12, phosphotungstic acid 13 etc.
  • Adipic Acid Route: Oxidation of Cyclohexene Vs. Cyclohexane

    Adipic Acid Route: Oxidation of Cyclohexene Vs. Cyclohexane

    catalysts Article Adipic Acid Route: Oxidation of Cyclohexene vs. Cyclohexane Ana P. C. Ribeiro 1 , Elisa Spada 2, Roberta Bertani 2 and Luísa M. D. R. S. Martins 1,* 1 Centro de Química Estrutural and Departamento de Engenharia Química, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, 1049-001 Lisboa, Portugal; [email protected] 2 Department of Industrial Engineering, University of Padova, 35122 Padova, Italy; [email protected] (E.S.); [email protected] (R.B.) * Correspondence: [email protected]; Tel.: +351-218-419-389 Received: 20 November 2020; Accepted: 8 December 2020; Published: 10 December 2020 Abstract: A cleaner alternative to the current inefficient oxidation of cyclohexane to adipic acid is presented. Direct oxidation of neat cyclohexene by aq. hydrogen peroxide to adipic acid is selectively achieved in good yield (46%), in the presence of the recyclable C-homoscorpionate iron(II) complex 3 [FeCl2{κ -HC(pz)3}] (pz = pyrazol-1-yl) and microwave irradiation, by a nitrous oxide-free protocol. Keywords: cyclohexene; adipic acid; oxidation; nitrous oxide; C-scorpionate; iron; microwave; ionic liquid; recyclable 1. Introduction Adipic acid (AA) is a highly relevant commodity produced at a large scale (over 3.5 mio metric tons/year and growing by ca. 5%/year) [1,2] worldwide, as it constitutes a building block for several industrial processes. It is mostly used for the synthesis of Nylon-6,6 polyamide; therefore, the rising demand for engineered plastics requires increased production of AA. Currently, adipic acid is mainly obtained by an inefficient and environmentally harmful two-step process [1,3] involving catalytic cyclohexane oxidation to cyclohexanol and cyclohexanone mixture followed by its oxidation with nitric acid.
  • Proposed Adipic Acid Production Protocol

    Proposed Adipic Acid Production Protocol

    ADIPIC ACID PRODUCTION PROJECT PROTOCOL Proposed Protocol October 26, 2019 ClimeCo Corporation One E Philadelphia Ave Boyertown, Pennsylvania 19512 (484) 415-0501 climeco.com Adipic Acid Production Project Protocol Prepared by: Bill Flederbach & James Winch, ClimeCo Corporation Version: 2.0 (Proposed Public Protocol) Version Date: 10/26/2019 This proposed protocol, initially developed by ClimeCo Corporation, is for use by the Climate Action Reserve in the development and evaluation process for a standardized offset project protocol reducing N2O emissions from adipic acid production. Contact Information: Bill Flederbach, Jr. ClimeCo Corporation One E Philadelphia Ave, Boyertown, Pennsylvania 19512 (484) 415-0501 [email protected] Tip Stama ClimeCo Corporation One E Philadelphia Ave, Boyertown, Pennsylvania 19512 (484) 415-0501 [email protected] i Adipic Acid Production Project Protocol Table of Contents 1. Introduction .......................................................................................................................................... 2 2. The GHG Reduction Project .................................................................................................................. 3 2.1. Background ............................................................................................................................... 3 2.2. Project Definition ...................................................................................................................... 4 2.3. The Project Developer .............................................................................................................